Time commitment: 6 minute read
Leaving your job feels like a pretty high stakes decision. Sometimes it’s easy — you get an opportunity that’s hard to refuse, have clearly outgrown your current role or are pivoting to an entirely different career path. But most of the time, it’s filled with nuance, confusion, and a lot of nerves. I’ve thought through this question a few times and discussed it with several Product Managers at various stages of their careers.
Should I start looking for another job or stay put? Is there something better for me out there?
I like to break the evaluation of this decision into a few buckets I call compatibility dimensions. Note that every one of these dimensions is highly person and situation dependent, so consider them one way to approach, not a “must follow:”
Lifestyle Compatibility
Before thinking through anything else, I ask myself if my current job is compatible with the lifestyle I want. I like to consider the average of the past three months and project the next three months to answer this question. As an example, if I’m commuting four hours a day and that’s starting to impact my health, the answer is probably no, this job is not compatible with the lifestyle I want. Even if I use a last/next three month average, it’s unlikely that my answer will change (I’ve probably been commuting like this for the last 3 months and can expect to do the same for the next 3+ months). Another example might be if I have been feeling extremely overwhelmed because of an upcoming product launch and that’s left me no time for family or hobbies. The answer to lifestyle compatibility seems like a no, but if you look at the next 3 months, things might calm down and change your answer. There are rough patches in every job, but it should average out to being mostly compatible with the lifestyle you want. A fair amount of weight should be applied to having a strong “yes” on lifestyle compatibility, but maybe “no’s” on other dimensions. Sometimes it’s OK to be “comfortable” and stay put because other parts of life are demanding more attention. Disclaimer: This is the most nuanced dimension and will be very different for everyone.
Story Compatibility
It’s a fairly common concept to PM your career like you PM your product. Every product needs strong positioning and the right narrative to find product-market-fit and win in the market. You need the same thing in your career. With that in mind, think about how much the current role you’re in is playing into your narrative or “story” as a PM. What unique experiences and skills are you gaining and/or what challenges are you getting the opportunity to solve? For example, if your ultimate goal is to take on a product leadership role in Big Tech then work backwards from that and identify the story that will get you there. Let’s say you have the opportunity to lead an end-to-end redesign of an entire product — this is very career additive! You are likely exercising product and design sense, leaning in heavily with users, managing a lot of stakeholders from across the company, and are laser focused on balancing any metric regressions. All things that are clearly beneficial to your journey to Big Tech. The takeaway here is that if your current role is helping to write an amazing chapter in your story then it’s “story compatible.” If it isn’t, then you may want to consider other options.
Manager Compatibility
A lot can be said on staying or leaving a job because of a good/bad manager. A few lines on this subject is unlikely to do it justice, but I’ll share my rough thoughts. At the core, your manager’s job is to provide the necessary context needed for you to drive impact in your role. They should coach you in improving both the hard and soft skills appropriate for your level of seniority. They should also be a sounding board and advocate for your career goals. Great managers do much more than this. They invest in their people, ensure psychological safety, build a strong relationship, and take the time to understand how someone can thrive in a way that’s good for the business and for the individual. Even though managers have a disproportionate impact on the success and even lives of their team, the truth is, most managers are not great managers. Your manager’s job description does not include making you happy, getting you promoted, or solving problems for you. The manager compatibility dimension is a deeply personal one to evaluate, but my general thought here is that neutral to positive is a “yes” while a very clearly negative manager experience means “no.”
Company Compatibility
Nikhyl Singhal explains this dimension quite well: if you feel like the company is growing slower than you are, it might be time to look elsewhere. Your company and the work that you support should be growing just a bit faster than you are growing. It should feel a little chaotic and fast-paced. This ensures that you’re operating at race pace and getting the right reps in to develop. This certainly does not mean that you’re making a mistake by staying at a company where growth (e.g., revenue growth, user growth, profitability etc.) is decelerating. That’s a normal part of the business cycle and actually might be a good environment to learn how to operate under pressure and turn things around. This is more around the company’s culture and the hustle, execution rigor, and confidence it instills, leading to continuous innovation, evolution, and growth. You’ll typically know pretty clearly if this dimension feels off.
Alternatives to Consider
Careers are long. Most of us are going to have a 30-40+ year career. When considering leaving a role, zoom out a bit and remember that you’re running a marathon not a sprint. Intentionally expanding your time horizon might help you make better decisions and not optimize for the short term.
Tenure matters more than you think, especially as you get more senior. It’s not terrible to leave a job after 1 or 2 years, but if you do that multiple times, this might be a bit of an eyebrow raise. Once you are more senior (e.g., Director+), it takes time to settle in and translate your strategy to real product/business impact. Because of that, barring any major red flags or things out of your control, 3 years is usually the minimum you should stay in a role before exploring something new
Leaving a job isn’t the only way to change it up. If your analysis on each of the above compatibility dimensions comes back less than ideal, your next step does not have to be quitting or immediately looking for another role. Have a conversation with a trusted leader, explore opportunities for internal mobility or changing the scope of your role, or think about taking a break.
Leaving a role to explore something new is never just a yes/no decision. There are a bunch of factors to consider. I hope the above guidance can help structure your thinking a bit!